AU2707192A - Substituted hydroquinone derivatives - Google Patents
Substituted hydroquinone derivativesInfo
- Publication number
- AU2707192A AU2707192A AU27071/92A AU2707192A AU2707192A AU 2707192 A AU2707192 A AU 2707192A AU 27071/92 A AU27071/92 A AU 27071/92A AU 2707192 A AU2707192 A AU 2707192A AU 2707192 A AU2707192 A AU 2707192A
- Authority
- AU
- Australia
- Prior art keywords
- halogen
- group
- lower alkyl
- formula
- unsubstituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 13
- 229910052736 halogen Inorganic materials 0.000 abstract 11
- 150000002367 halogens Chemical class 0.000 abstract 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 10
- 125000003545 alkoxy group Chemical group 0.000 abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract 7
- 239000001257 hydrogen Substances 0.000 abstract 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 7
- -1 benzyloxy, phenyl Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 4
- 125000001424 substituent group Chemical group 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 abstract 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 1
- 229940006460 bromide ion Drugs 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4056—Esters of arylalkanephosphonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5456—Arylalkanephosphonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/59—Hydrogenated pyridine rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Neurosurgery (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Veterinary Medicine (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Inorganic Insulating Materials (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Compounds of the formula I
<IMAGE>
in which R4 is lower alkyl and R1 is either hydroxyl, halogen, a group of the formula -P(=O)(R5)R6 (Ia), a group of the formula -P<+)<R7)(R8)R9X <-> (Ib) or a group of the formula -Si(R7)(R8)R9 (Ic), M is methylene, R2 is hydrogen or a group of the formula
<IMAGE>
and R3 is hydrogen or halogen or R1 is hydroxyl or lower alkoxy, M is carbonyl, R2 is hydrogen and R3 is halogen, R5 and R6 in each case independently of one another represent lower alkyl, lower alkoxy, N,N-di-lower alkylamino or benzyl, benzyloxy, phenyl or phenoxy, each of which is unsubstituted or mono- or disubstituted on the phenyl ring, it being possible for the substituents of the phenyl ring in each case to be selected from the group which consists of lower alkyl, lower alkoxy, nitro and halogen, R7, R8 and R9 in each case independently of one another represent lower alkyl, unsubstituted or mono- or disubstituted phenyl, it being possible for the substituents of the phenyl ring in each case to be selected from the group which consists of lower alkyl, lower alkoxy, nitro and halogen, or represent furyl, X<-> is the anion of a hydrohalic acid, a lower alkane-sulphonic acid, a halo-lower alkanesulphonic acid or a benzenesulphonic acid which is unsubstituted or monosubstituted by lower alkyl or halogen and in which Y either represents a direct bond and R10 is lower alkyl, allyl, cyano, lower alkanesulphonyl, halo-lower alkanesulphonyl, benzyl which is unsubstituted or mono- or disubstituted on the phenyl ring, it being possible for the substituents of the phenyl ring to be selected from the group which consists of lower alkyl, lower alkoxy, nitro and halogen, or is benzenesulphonyl which is unsubstituted or monosubstituted by lower alkyl or halogen, or in which Y is a group of the formula -(C=O)- (Ie) or a group of the formula -(C=S)- (If) and R10 is halogen, lower alkyl, halo-lower alkyl, lower alkoxy, lower alkenyloxy, phenyl-lower alkenyloxy, halo-lower alkoxy, lower alkylthio or phenyl, phenoxy, phenylthio, benzyl, benzyloxy or benzylthio, each of which is unsubstituted or mono-or disubstituted on the phenyl ring, it being possible for the substituents of the phenyl ring in each case to be selected from the group which consists of lower alkyl, lower alkoxy, nitro and halogen, with the proviso that in a compound I in which R1 is a group Ib in which R7, R8 and R9 in each case denote unsubstituted phenyl and X<-> is the bromide ion, M is methylene, R2 is hydrogen and R4 is methyl, R3 is other than hydrogen, and with the further proviso that in a compound I in which R1 is hydroxyl, M is methylene, R2 is hydrogen and R4 is methyl or ethyl, and R3 is other than hydrogen, can be used for the preparation of compounds of the formula
<IMAGE>
in which R3 is halogen and R4 is lower alkyl and R10 and Y have the abovementioned meanings, and their salts. They are prepared by methods known per se.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH3042/91 | 1991-10-17 | ||
| CH304291 | 1991-10-17 |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU36614/95A Division AU691344B2 (en) | 1991-10-17 | 1995-11-02 | Substituted hydroquinone derivatives |
| AU36615/95A Division AU691345B2 (en) | 1991-10-17 | 1995-11-02 | Substituted hydroquinone derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2707192A true AU2707192A (en) | 1993-04-22 |
| AU661722B2 AU661722B2 (en) | 1995-08-03 |
Family
ID=4247322
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU27071/92A Ceased AU661722B2 (en) | 1991-10-17 | 1992-10-15 | Substituted hydroquinone derivatives |
| AU36614/95A Expired - Fee Related AU691344B2 (en) | 1991-10-17 | 1995-11-02 | Substituted hydroquinone derivatives |
| AU36615/95A Expired - Fee Related AU691345B2 (en) | 1991-10-17 | 1995-11-02 | Substituted hydroquinone derivatives |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU36614/95A Expired - Fee Related AU691344B2 (en) | 1991-10-17 | 1995-11-02 | Substituted hydroquinone derivatives |
| AU36615/95A Expired - Fee Related AU691345B2 (en) | 1991-10-17 | 1995-11-02 | Substituted hydroquinone derivatives |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US5290939A (en) |
| EP (1) | EP0542671B1 (en) |
| JP (1) | JPH05213808A (en) |
| KR (1) | KR930007940A (en) |
| AT (1) | ATE147059T1 (en) |
| AU (3) | AU661722B2 (en) |
| CA (1) | CA2080683A1 (en) |
| DE (1) | DE59207805D1 (en) |
| DK (1) | DK0542671T3 (en) |
| ES (1) | ES2096062T3 (en) |
| FI (1) | FI924651A (en) |
| GR (1) | GR3022221T3 (en) |
| HU (1) | HUT62250A (en) |
| IL (1) | IL103447A0 (en) |
| MX (1) | MX9205989A (en) |
| NO (1) | NO180441C (en) |
| NZ (1) | NZ244751A (en) |
| RU (1) | RU2095339C1 (en) |
| TW (1) | TW209869B (en) |
| ZA (1) | ZA928003B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5693807A (en) * | 1992-10-14 | 1997-12-02 | Ciba-Geigy Corporation | Substituted hydroquinone derivatives |
| DE69418789T2 (en) * | 1993-08-05 | 1999-12-02 | Hoechst Marion Roussel, Inc. | 2- (Piperidin-4-yl, pyridin-4-yl and tetrahydropyridin-4-yl) benzofuran-7-carbamate derivatives, their preparation and use as acetylcholinesterase inhibitors |
| CN100546970C (en) * | 2006-05-18 | 2009-10-07 | 中国科学院广州化学研究所 | A kind of synthetic method of bromo benzoic ether |
| CN104769006B (en) | 2012-09-07 | 2017-03-08 | 英派尔科技开发有限公司 | Regioregular copolymer and preparation method thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4600719A (en) * | 1973-03-02 | 1986-07-15 | Ciba Geigy Corporation | Tetrahydropyridine and piperidine derivatives |
| CH592656A5 (en) * | 1973-03-02 | 1977-10-31 | Ciba Geigy Ag | |
| CH609054A5 (en) * | 1975-11-26 | 1979-02-15 | Ciba Geigy Ag | Process for the preparation of a novel piperidine derivative |
| JPS63139180A (en) * | 1986-12-02 | 1988-06-10 | Tanabe Seiyaku Co Ltd | Carboxylic acid derivative |
| FR2619111B1 (en) * | 1987-08-07 | 1991-01-11 | Synthelabo | (PIPERIDINYL-4) METHYL-2 TETRAHYDRO-1,2,3,4 9H-PYRIDO (3,4-B) INDOLE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION |
| FR2626877B1 (en) * | 1988-02-05 | 1991-04-05 | Delalande Sa | ALKYLIC OR BENZYL ETHERS OF PHENOL, PROCESSES FOR THEIR PREPARATION AND THEIR APPLICATION IN THERAPEUTICS |
| EP0352581A3 (en) * | 1988-07-28 | 1990-07-04 | F. Hoffmann-La Roche Ag | Ethylene diaminmonoamide derivatives |
-
1992
- 1992-09-03 RU SU925053216A patent/RU2095339C1/en active
- 1992-10-08 DK DK92810768.9T patent/DK0542671T3/en active
- 1992-10-08 ES ES92810768T patent/ES2096062T3/en not_active Expired - Lifetime
- 1992-10-08 DE DE59207805T patent/DE59207805D1/en not_active Expired - Fee Related
- 1992-10-08 AT AT92810768T patent/ATE147059T1/en not_active IP Right Cessation
- 1992-10-08 EP EP92810768A patent/EP0542671B1/en not_active Expired - Lifetime
- 1992-10-09 TW TW081108038A patent/TW209869B/zh active
- 1992-10-14 US US07/961,001 patent/US5290939A/en not_active Expired - Lifetime
- 1992-10-14 HU HU9203233A patent/HUT62250A/en unknown
- 1992-10-14 FI FI924651A patent/FI924651A/en not_active Application Discontinuation
- 1992-10-15 NZ NZ244751A patent/NZ244751A/en unknown
- 1992-10-15 IL IL103447A patent/IL103447A0/en unknown
- 1992-10-15 AU AU27071/92A patent/AU661722B2/en not_active Ceased
- 1992-10-15 CA CA002080683A patent/CA2080683A1/en not_active Abandoned
- 1992-10-16 ZA ZA928003A patent/ZA928003B/en unknown
- 1992-10-16 JP JP4278265A patent/JPH05213808A/en active Pending
- 1992-10-16 NO NO924024A patent/NO180441C/en unknown
- 1992-10-16 KR KR1019920019147A patent/KR930007940A/en not_active Application Discontinuation
- 1992-10-16 MX MX9205989A patent/MX9205989A/en unknown
-
1995
- 1995-11-02 AU AU36614/95A patent/AU691344B2/en not_active Expired - Fee Related
- 1995-11-02 AU AU36615/95A patent/AU691345B2/en not_active Expired - Fee Related
-
1997
- 1997-01-03 GR GR960403661T patent/GR3022221T3/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU691344B2 (en) | 1998-05-14 |
| DE59207805D1 (en) | 1997-02-13 |
| RU2095339C1 (en) | 1997-11-10 |
| NO924024D0 (en) | 1992-10-16 |
| AU3661595A (en) | 1996-01-11 |
| AU691345B2 (en) | 1998-05-14 |
| KR930007940A (en) | 1993-05-20 |
| ATE147059T1 (en) | 1997-01-15 |
| US5290939A (en) | 1994-03-01 |
| NO924024L (en) | 1993-04-19 |
| DK0542671T3 (en) | 1997-01-20 |
| FI924651A (en) | 1993-04-18 |
| GR3022221T3 (en) | 1997-04-30 |
| MX9205989A (en) | 1993-08-31 |
| HU9203233D0 (en) | 1992-12-28 |
| CA2080683A1 (en) | 1993-04-18 |
| EP0542671B1 (en) | 1997-01-02 |
| FI924651A0 (en) | 1992-10-14 |
| ES2096062T3 (en) | 1997-03-01 |
| NO180441C (en) | 1997-04-23 |
| EP0542671A1 (en) | 1993-05-19 |
| NO180441B (en) | 1997-01-13 |
| AU3661495A (en) | 1996-01-04 |
| JPH05213808A (en) | 1993-08-24 |
| IL103447A0 (en) | 1993-03-15 |
| TW209869B (en) | 1993-07-21 |
| AU661722B2 (en) | 1995-08-03 |
| ZA928003B (en) | 1993-04-19 |
| NZ244751A (en) | 1995-02-24 |
| HUT62250A (en) | 1993-04-28 |
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